
House holiday rentals in Chesterfield
Find and book unique houses on Airbnb
Top-rated house rentals in Chesterfield
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterfield house rentals
House rentals with a pool

Large Modern Décor 3 Bed with Driveway & Garden
Lovely cosy house which was clean and tidy. This was our second stay at Homestead and we will be coming back.

Ashbourne Cottage near Dovedale
Really good place stay, easy to find. Had a great time!

Love Nest - an intimate hideaway
our stay at staycation cottages in bakewell was lovely. the love nest Lodge was very quaint and well equipped. the bathroom was especially layed out nicely. I enjoyed the access to the football playing area, pool area and the swimming pool. we used the bbq area once and made full use of the boot room for leaflets and information for our stay would definitely return back

Grove Farm Cottage
Lovely stay, the farm was beautiful and the animal feeding was the highlight of our childrens’ stay. Pool was great, super clean everywhere, and they provided maps of local walks which we utilised too. Couldn’t have asked for much more.

Peak District Manor: Pool + Hot Tub + Fire Pit
The house was absolutely incredible and excellent value for money. It was in stunning surroundings, the hot tub was amazing and the exclusive booking system for use of the pool was a lovely addition. The house was spotless and full of character and the private garden was also wonderful. The beds were really comfortable and there was just the right balance of charm, space and comfort. We definitely struck gold when booking this gem. Thanks so much for all of your support in making this a trip to remember!

The Manor House
What a wonderful stay at Manor Farm. The house was beautiful, well maintained, extremely spacious and very comfortable. The surrounding countryside was stunning, with great food being served in nearby pubs and plenty of places to visit. Great space for youngsters too, with the wildlife - baby rabbits, sheep and birds and of course the swimming pool and games room, all of which they loved. Thanks to the hosts for their welcome and hospitable atmosphere.

Badgers Wood
Great value for money. Can't stress enough how friendly and reliable the staff were. We had a lovely week stay, the house was clean, the beds were comfy and the scenery was perfect. We were informed of the booking system for the swimming pool and games room, so you could have the room to yourself which was great. The pool was clean, the games room was kept tidy and the house surroundings were really lovely to walk around. You can tell the grounds were well maintained and kept in good shape as the workers never stopped, but were always so friendly. This property is perfect for bike riders, walkers and pub crawlers. You couldn't get bored.

Pippinwell
Me and my family really enjoyed our stay! The place was clean and there was plenty of space for all 8 of us (and our dog!). The area is stunning, very quiet with plenty of nice walks. The pool/games room area is shared with the other cottages, which wasn't made clear when booking. We thought it was part of our cottage, which we were slightly disappointed to find out this wasn't the case. However, overall we'd still consider staying here again!
Weekly house rentals

Lovely house Eckington Sheffield
Lovely clean and cosy house. Great communication

Chert Cottage, Great Longstone, Bakewell Peak Dist
We had a lovely, long weekend stay at Chert cottage. Great Longstone is an excellent location, with several pubs within walking distance. Beautiful scenery is on the doorstep, with places like Bakewell and Buxton a short drive away. Sarah was an excellent host - she was very responsive and we really appreciated the cake, milk and flowers on arrival. Chert cottage itself was great - very clean and equipped with everything you could possibly need - we particularly loved sitting out in the garden in the evening! Many thanks Sarah, we had a great time.

The Cottage - Derbyshire
We (3 friends) had a really nice stay here. The house was very clean and well looked after and the views from the front of the house just amazing. Comfy beds, plenty of parking and the kitchen had everything we needed. Great location too for our visits to Bolsover Castle and Renishaw gardens.

Highfield House - Rural Retreat Derbyshire
A wonderful house in a quiet location. Lovely pubs and country walks on your doorstep! Hot tub a great bonus, ideal for our reunion weekend. Thank you Penny... perfect :-)

Cosy 2 bed home CHESTERFIELD
Me and my partner visited over Valentines weekend and were so pleased with the accommodation, it was easy to find and located in a lovely town with lots of pubs and takeaway options. Everything from the decor and furniture to the facilities available were brilliant, the house was spotless and we couldn’t find a single thing to complain about. Thoroughly enjoyed our stay and would happily return in the future x

Riverbank Cottage - Annex
Booked this trip last minute and was not disappointed with our choice, the instructions for parking and how to find the cottage was spot on. Less then a couple minutes walk and you’re at all the coffee shops and pubs with a short drive to other villages and all the famous walks.

Blissful Barry’s
A comfortable and well appointed Airbnb in a lovely peaceful area. Host was always quick to respond to any questions and the whole process was easy and efficient. Would definitely recommend to anyone looking to stay near Chesterfield but in a more relaxed area!

Commuters Getaway Chesterfield
we have just spent 5 days there would recommend it.Dan was very helpful .The house is very central for exploring the Peak District and is a nice walk into Chesterfield about 20 minutes, plenty of pubs to choose for meals .
Private house rentals

Luxury manor house with hot tub
We loved our stay at Gill and Steve’s. It’s one of the nicest we have ever stayed in. My husband and I plus 8 of our friends stayed for two nights. We had so much fun!!! The outside space is perfect for dinners and drinks. The house is huge and has everything we needed. Gill and Steve are amazing hosts. Such good people and were so responsive and helped us to make a lovely weekend for our friends. Enough parking for all 5 couples to drive!! Will be back!! :)

Detached Converted Farmhouse, Mosborough, S20
A beautiful house, and a great host. The property was just like the description and photos. Great for us as we have family close by. Dean was brilliant at keeping in touch and came back whenever I messaged him. Will certainly book again. Thank you for an amazing stay.

Elegant and exclusive Manor House stay, Derbyshire
We had an absolutely wonderful stay at Salli’s place. The house itself is stunning, spacious, beautifully decorated, and equipped with everything we needed for a comfortable and relaxing trip. It’s also perfectly located, with easy access to some fantastic hiking trails nearby, which we really enjoyed exploring. Salli was an excellent host—friendly, responsive, and incredibly helpful throughout our stay, making sure we had everything we needed. We would highly recommend this property to anyone looking for a peaceful getaway in a beautiful setting. Thank you, Salli, for hosting us!

1 Bedroom Terrace in Quiet area
I stayed at Sams place for almost two months and it was one of the best decisions ever. The house is very well done and in a very nice and safe location. It is close to bus stops and the royal hospital. Sam replied almost immediately if I had any questions or doubts. The house is spacious and with a very nice backyard as well. I'm glad I could this place a home for 2 months. I would highly recommend Sams place for anyone looking to stay in Chesterfield for short/long term.

Fox Cottage at Yew Tree Farm
A very nice cottage in an excellent location. Very clean with all amenities included. Lots of attractions very close by. Highly recommended Homemade jam much appreciated We really enjoyed our stay!

Lovely 3 Bedroom house - great location
We used this lovely home while waiting for the purchase of our new home to complete, we wanted somewhere in Chesterfield that was going to feel like a home and be comfortable while I’m undergoing chemo, Winston’s home ticked every box and our 2 dogs and 2 house cats definitely approved, the garden is secure and safe, parking outside was perfect, we couldn’t have picked a better property, even suppling a Christmas tree and decorations made it that much more special, thank you 🙏

Lily's Cottage
Great house with everything we needed. Great value

Hugo’s Luxury Barn
This place is truly beautiful the surroundings are incredible the place is beautiful, garden was lovely and the barn was perfect I would definilty recommend and it was amazing value for money
Quick stats about house rentals in Chesterfield
Total rentals
60 properties
Nightly prices starting at
$50 NZD before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Manchester Holiday rentals
- Leeds and Liverpool Canal Holiday rentals
- Cheshire Holiday rentals
- Yorkshire Holiday rentals
- Darwen Holiday rentals
- Birmingham Holiday rentals
- Liverpool Holiday rentals
- North Wales Holiday rentals
- Cotswold District Holiday rentals
- Cotswolds Holiday rentals
- Oxford Holiday rentals
- River Thames Holiday rentals
- Rentals with outdoor seating Chesterfield
- Cabin rentals Chesterfield
- Cottage rentals Chesterfield
- Family-friendly rentals Chesterfield
- Rentals with a washing machine and dryer Chesterfield
- Rentals with a fireplace Chesterfield
- Apartment rentals Chesterfield
- Condo rentals Chesterfield
- Pet-friendly rentals Chesterfield
- Rentals with a patio Chesterfield
- House rentals Derbyshire
- House rentals England
- House rentals United Kingdom
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Peak District national park
- Alton Towers
- Peak District
- The Quays
- Etihad Stadium
- Chatsworth House
- Drayton Manor Theme Park
- Tatton Park
- Lincoln Castle
- Harewood House
- Sundown Adventureland
- Mam Tor
- IWM North
- Crucible Theatre
- Royal Armouries Museum
- Holmfirth Vineyard
- Cavendish Golf Club
- Shrigley Hall Golf Course
- The Nottinghamshire Golf & Country Club
- John Rylands Library
- Derwent Valley Mills
- Rufford Park Golf and Country Club
- Manchester Central Library
- Bosworth Battlefield Heritage Centre